1. Field of Invention
This invention relates to aryl oxo-alkynoates, intermediates and processes for their preparation, pharmaceutical compositions containing them and pharmaceutical methods using them.
2. Prior Art
U.S. Pat. No. 4,405,810 issued Sept. 20, 1983 to Blythin et al. discloses 7-arylhept-5-ynoic acids and derivatives thereof as anti-allergy and antiinflammatory agents. These compounds have the formula: ##STR2## where
R.sub.1 is H, lower alkyl or phenyl, and
Aryl is naphthyl or ##STR3## where R includes H, phenyl, alkyl, phenoxy, and phenyl (CH.sub.2).sub.m where m is 0-2.
U.S. Pat. No. 3,839,455 issued Oct. 1, 1974 to Scherm and Peteri discloses 1-alkenyl-2-benzoyl-acetylenes of the formula ##STR4## wherein R.sup.1 and R.sup.2 can be alike or different and can be hydrogen or lower alkyl containing 1 to 6 carbon atoms; X is halo and n=0-5, preferably 0-2. These compounds are disclosed as having fungistatic and bacteriostatic activity.
U.S. Pat. No. 3,592,922 issued July 13, 1971 to Gier and Calhoon discloses acetylenic ketones of the formula ##STR5## wherein R.sup.1 is ethyl or phenyl and R.sup.2 is lower alkyl, phenyl, alkylphenyl, phenylethenyl, benzyl, halophenyl, alkenyl or halophenoxymethyl. The compounds are disclosed as plant fungicides and nematocides.
U.S. Pat. No. 3,812,262 issued to Chodnekar et al. on May 21, 1974 discloses substituted propiolophenones of the formula ##STR6## where R.sup.1 and R.sup.2 are hydrogen, hydroxy, halogen, lower alkyl, lower alkoxy or propynyloxy or together represent a lower alkylenedioxy group with the condition that both are not hydrogen. These compounds are disclosed as plant fungicides, nematocides, and insecticides.
T. Fukumaru et al. in Agr. Biol. Chem., 39, 519(1975) disclose acetylenic ketone compounds having antiinflammatory and antimicrobial activity.
M. M. Midland et al. in J. Am. Chem. Soc., 102, 867 (1980) describe the reduction of .alpha.,.beta.-acetylenic ketones. No biological activity for these compounds is disclosed.
H. Durr et al. in Justus Liebigs Ann Chem., 7, 1140 (1974) describe the formation of N-heterocycles by the 1,3 dipolar cycloaddition of a diazofluorene with alkynes of the formula EQU R.sup.4 C.tbd.CR.sup.5
where R.sup.4 is Me, COMe, COPh or CO.sub.2 Me and R.sup.5 is NEt.sub.2, CHMeOH, COMe, COPh or CO.sub.2 Me. No biological activity for these alkynes is disclosed.
Acetylenic ketones are also disclosed as substrates in chemical reactions by H. Saikach et al., Chem. Pharm. Bull., 27, 2857 (1979) and J. Bastide et al., Tetrahedron Lett., 41, 4225 (1972).
Acetylenic ketones, useful for the production of heterocyclic compounds used as intermediates for the production of pharmaceuticals and agrochemicals are disclosed in Japanese Patent 5707291 issued May 7, 1982.
Co-assigned U.S. patent application Ser. No. 650,187 filed on Sept. 13, 1984 discloses aryl alkynes as 5-lipoxygenase inhibitors, of the general formula ##STR7##